The Snowbird Circuit

 Conventional wisdom is that the average medieval commoner did not travel very far in their lifetime. While it would certainly not be unusual for someone to have never seen more than fifteen miles outside their home village, there was quite a few means for travel, and a lot of incentive to do so, as Medieval Americans could see a wide variety of climate--harsh, snowy summers in the north and humid, steaming summers in the south. With little in the way of oil or air conditioners to mitigate that. For those who could manage, there  are a few ways to get around that.

Entertainment: As mentioned before, members of the noble class tend to hold tournaments. The season starts at roughly the end of a Harvest season, where people have time to watch it, and the circuit will sort of outrun the cold, until the last championships somewhere around January, usually called the Super Bowl. With them follow the smiths, merchants, prostitutes, and just about any industry that would pop up when a city of tournament tents takes root. This is also sometimes the plan for travelling entertainers, though some seek to swim upstream, knowing that castles and communities that are cooped up and bored during the winter might be more welcoming to someone who's wares are song and cheer. 

Pilgrimage: Pilgrimages were common in the Middle Ages, usually to visit the most prestigious monasteries, and during the core of the Middle Ages, it was imperative to visit the Holy Land. Americans certainly recognize the significance of the Holy Land, but are extremely unlikely to ever see it, so they hold pilgrimages to places significant to the American Church. In the warmer months they include Plymouth and  Rhode Island, (Near Cape Cod and Newport, very popular destinations to cool off in the Industrial Age) to Philadelphia (where the Declaration was signed)  to Washington D.C. (the capital of the Non-Denom world) to Jacksonville (Near St. Augustine, the first place in America to be colonized.) Fairly convenient, really. 

Warfare: One can always just embark on a military career--this being a Medieval society--there aren't a lot of standing armies in Medieval America, but compared to Europe, there are a lot of mercenary bands. The Northern states do not like to engage in warfare in the winter months, when fights are still going on a relatively short distance away, so the mercenary industry is able to keep busy fairly often. But even outside of the threat of being slain in battle, it's generally not as smooth as the pilgrimage of the Eastern seaboards, who are very much invested in keeping their path of providence from turning into a war zone. Still, some are more inclined, or just better, and taking the plundering and pillaging path to getting a little sun, than quiet contemplation in a monastery.